(R)-3-Hydroxy-3-(2-methoxy-3-methoxymethoxymethyl-pyridin-4-yl)-pentanoic acid | 472958-61-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-Hydroxy-3-(2-methoxy-3-methoxymethoxymethyl-pyridin-4-yl)-pentanoic acid
• 英文别名: (3R)-3-hydroxy-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentanoic acid
• CAS: 472958-61-5
• 化学式: C₁₄H₂₁NO₆
• 分子量: 299.324
• InChiKey: GWWIQDHIFCYLRN-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98.11
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-3-Hydroxy-3-(2-methoxy-3-methoxymethoxymethyl-pyridin-4-yl)-pentanoic acid 在 三甲基氯硅烷 、 水 、 三氟乙酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 31.0h， 生成 5-乙基-5-羟基-1,4,5,8-四氢氧杂卓并[3,4-c]吡啶-3,9-二酮
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4
• 作为产物：
  描述：

  (-)-3-hydroxy-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentanal 在 sodium chlorite 、 disodium hydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 36.0h， 生成 (R)-3-Hydroxy-3-(2-methoxy-3-methoxymethoxymethyl-pyridin-4-yl)-pentanoic acid
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4